53 Highland Drive, Monroe, CT 06468
OFF MARKET

53 Highland Drive
Monroe, CT 06468

East Village
  • 2 Beds
  • 1.5 Baths
  • 1,011 sqft

$396,700

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $2,621/mo*

$396,700

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $2,621/mo*
2 Beds
1.5 Baths
1,011 sqft

Local Information

  • Map ViewExplore the area around 53 Highland Drive.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Welcome to High Meadows! Monroe's 55+ Community is located on the Eastern edge of Connecticut's Fairfield County! Miles away from the Housatonic River's historic Stevenson Dam. Short drive to the NY border 23 miles+/- of Brewster on CT-I-84 and only 46 miles +/- I-95. This is an END-UNIT 1 Bedroom with 1.5 bathroom condo that hasn’t hit the market in over 20 years! Additional finished upper and lower levels with mechanical room for plenty of storage/workshop space. Washer and dryer on the main floor. Attached 1 car garage with additional parking. Clubhouse. Close to restaurants, entertainment, family farms/wine vineyards, ice cream shops, retail/food shopping, health care facilities/gyms and so much more! Come live in Monroe - a small town with New England charm!
53 Highland Drive, Monroe, CT 06468 is a 2 bedroom, 2 bathroom, 1,011 sqft condo in East Village, built in 1995. It last sold for $374,000 on Jul 7, 2025 (10% above the $339,000 asking price). It is currently off market. The Trulia Estimate is $396,700, with a rent estimate of $2,876/month.

Home Highlights

Parking
1 Car Garage
Outdoor
Porch, Patio
A/C
Heating & Cooling
HOA
$489/Monthly
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 53 Highland Drive

Interior Features

Interior Details
Basement: Partially Finished,Heated,Cooled,Storage SpaceNumber of Rooms: 4Types of Rooms: Master Bedroom, Bedroom, Bathroom, Dining Room, Family Room, Kitchen, Loft, Rec Play Room
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1011 Square Feet
Appliances & Utilities
Appliances: Electric Cooktop, Electric Range, Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Electric Water HeaterDishwasherDryerLaundry: Mud RoomRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,ElectricHas CoolingAir Conditioning: Ceiling Fan(s),Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Common Walls: End Unit
Levels, Entrance, & Accessibility
Stories: 3Accessibility: Bath Grab Bars, Raised Toilet

Exterior Features

Exterior Home Features
Patio / Porch: Patio, Porch, EnclosedExterior: Rain Gutters, SidewalkNo Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageHas an Attached GarageParking Spaces: 1Parking: Attached,Garage Door Opener
Frontage
Not on Waterfront
Water & Sewer
Sewer: Shared Septic
Finished Area
Finished Area (above surface): 1011 Square Feet

Property Information

Year Built
Year Built: 1995
Property Type / Style
Property Type: ResidentialProperty Subtype: Condominium, ApartmentStructure Type: ApartmentArchitecture: Ranch,Apartment
Building
Building Name: High MeadowsConstruction Materials: Shingle Siding, Wood SidingNot a New ConstructionAttached To Another StructureDoes Not Include Home Warranty
Property Information
Not Included in Sale: Refer to Inclusion/ExParcel Number: 179229

Price & Status

Price
List Price: $339,000
Status Change & Dates
Off Market Date: Wed Aug 23 2023Possession Timing: Withheld

Active Status

MLS Status: Closed

Location

Direction & Address
City: MonroeCommunity: East Village
School Information
Elementary School: Per Board of EdJr High / Middle School: Per Board of EdHigh School: Masuk

Building

Building Area
Building Area: 1011 Square Feet

Community

Community Features: Adult Community 55, Golf, Lake, Library, Medical Facilities, Park, Public Rec Facilities, Shopping/MallIs a Senior Community

HOA

HOA Fee Includes: Maintenance Grounds, Trash, Snow RemovalHas an HOAHOA Fee: $489/Monthly

Miscellaneous

BasementMls Number: 170591678Attic: Walk-up, Finished, StorageAbove Grade Unfinished Area: 1011

Additional Information

HOA Amenities: Clubhouse,Management
Last check for updates: about 1 hour ago
Listed by Stephen Thrower, (203) 543-3438
Realty ONE Group Connect, (203) 590-1111
Bought with: Marissa Papa, (203) 331-7043, Preston Gray Real Estate, (475) 269-5100
Source: Smart MLS, MLS#170591678

Price History for 53 Highland Drive

DatePriceEventSource
07/07/2025$374,000Sold
N/A
10/20/2023$355,000Sold
Smart MLS #170591678
08/16/2023$339,000Listed For SaleSmart MLS #170591678
05/10/1995$139,900Sold
N/A

Market trends in Monroe

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
63
23
MoM
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Property Tax and Assessment

Year2025
Tax$6,818
Assessment$237,800
Home facts updated by county records

Comparable Sales for 53 Highland Drive

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.08
Condo
$360,000
02/24/26
2
2.5
1,011
0.16
Condo
$329,900
01/06/26
1
1.5
1,011
0.06
Condo
$390,000
07/29/25
1
2.5
1,631
0.14
Condo
$362,000
09/26/25
1
1.5
2,011
2.45
Condo
$420,000
05/27/26
2
3
2,204

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Assigned Schools

These are the assigned schools for 53 Highland Drive.
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Neighborhood Overview

Neighborhood stats provided by third party data sources.

LGBTQ Local Legal Protections

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Homes for sale near 53 Highland Drive

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Off Market Homes Near 53 Highland Drive

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